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Amino Acids

Hardchemistry

A certain alpha-amino acid has a side chain bearing an extra carboxyl group, giving it three ionisable groups in total. How will its isoelectric point compare with that of a simple neutral amino acid like glycine?

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About This Question

Subject
chemistry
Chapter
biomolecules
Topic
amino acids
Difficulty
Hard
Year
2025
Tags
acidic amino acidisoelectric pointside chain carboxylnet chargeionisation

Solution

Correct Answer:

It will be lower because the acidic side chain shifts the neutral pH downward

The isoelectric point is the pH at which an amino acid carries zero net charge, and its value is set by the balance of all ionisable groups present. In glycine, only the alpha-carboxyl and alpha-amino groups ionise, and the zero-charge condition is met near pH 6. An acidic amino acid such as aspartic or glutamic acid carries an additional carboxyl group on its side chain; this extra acidic group tends to lose a proton and acquire negative charge, so a more acidic environment (a lower pH with higher hydrogen-ion concentration) is required to suppress that ionisation and bring the net charge to zero. Consequently the isoelectric point is shifted to a lower pH than glycine, making the first option correct. The claim that an extra carboxyl adds basic character is chemically backwards, since carboxyl groups are acidic, so the higher-pH option is wrong. The isoelectric point cannot be identical to glycine because the group balance has changed, and three ionisable groups can certainly define a net-zero pH, so it is not undefined. This follows the NCERT idea of acidic and basic amino acids. As a plausibility check, basic amino acids with extra amino groups instead show raised isoelectric points, confirming the trend works in the expected opposite direction.

This hard difficulty chemistry question is from the chapter biomolecules, covering the topic of amino acids. It appeared in the 2025 exam.

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